The entrepreneurial environment in Ukraine is beginning to emerge under the influence of the shock of the transition period associated with the mass release of workers and employees, the collapse of the financial system, the lack of national currency, and, consequently, the lack of funds for people’s livelihood. The article raises a range of issues related to the dilemma of “state support – self-regulation” of entrepreneurial structures, which, despite their constant presence on the policy agenda, find separate solutions at different stages of societal development. The paper notes that the differences in regional development have also affected the state of the entrepreneurial environment at the regional level and the set of measures to support small and medium-sized enterprises (SMEs). The article analyzes SME support programs at the level of the Poltava region and highlights their positive and negative aspects. It is concluded that the regional SME support programs’ positive results are due to factors such as linking financial assistance to the number of jobs created and cooperation of the city SME representatives with NGOs, Poltava City Council, and PROMIS project representation in the region. Attention is paid to the activity of the Regional Fund for Entrepreneurship Support, reflecting the specifics of the economy of the Poltava region. The necessity of new approaches to improve the state support of small and medium-sized enterprises, considering the war risks, conditions of post-war recovery, and the limited state budget, was substantiated. In this context, it is recommended to strengthen the capacity of entrepreneurship through the self-organization of entrepreneurs by creating business associations. It is noted that the associations already registered during the study are actively cooperating with state institutions to improve the conditions for their own economic activity. The proposals and conclusions formulated in the article can be helpful for regional public authorities in forming and implementing SME support policy, as well as individual programs to support and stimulate SME development. Keywords: support, small and medium entrepreneurship, public authorities, program, development, interaction.